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Molecules in the title compound, C
19H
17N
5, are linked into chains
via weak C—H
π(cyano) interactions, and these chains are linked
via C—H
π(arene) interactions to form a three-dimensional structure of parallel sheets.
Supporting information
CCDC reference: 610909
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.072
- wR factor = 0.141
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C15 .. 5.05 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C7 .. 5.10 su
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C7 ... 1.44 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).
4-{3,5-Dimethyl-4-[(
E)-(4-methylphenyl)diazenyl]-1
H-pyrazol-1-yl}benzonitrile
top
Crystal data top
C19H17N5 | Z = 2 |
Mr = 315.38 | F(000) = 332 |
Triclinic, P1 | Dx = 1.279 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3464 (18) Å | Cell parameters from 632 reflections |
b = 9.4021 (18) Å | θ = 2.1–26.4° |
c = 10.422 (2) Å | µ = 0.08 mm−1 |
α = 108.580 (3)° | T = 273 K |
β = 98.301 (4)° | Plate, orange |
γ = 103.722 (4)° | 0.45 × 0.13 × 0.06 mm |
V = 818.9 (3) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | Rint = 0.046 |
φ and ω scans | θmax = 26.4°, θmin = 2.1° |
6660 measured reflections | h = −11→11 |
3312 independent reflections | k = −11→11 |
1932 reflections with I > 2σ(I) | l = −13→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0414P)2] where P = (Fo2 + 2Fc2)/3 |
3312 reflections | (Δ/σ)max = 0.011 |
220 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.6651 (3) | 0.8449 (4) | 1.3463 (3) | 0.0949 (14) | |
N2 | 0.7970 (2) | 0.6548 (3) | 0.7017 (2) | 0.0466 (8) | |
N3 | 0.9120 (2) | 0.7625 (3) | 0.6813 (2) | 0.0506 (8) | |
N4 | 0.7662 (2) | 0.4340 (3) | 0.3516 (2) | 0.0493 (9) | |
N5 | 0.8331 (2) | 0.4728 (3) | 0.2666 (2) | 0.0505 (9) | |
C1 | 0.7153 (3) | 0.7760 (3) | 1.1005 (3) | 0.0483 (11) | |
C2 | 0.8591 (3) | 0.8320 (3) | 1.0820 (3) | 0.0489 (10) | |
C3 | 0.8843 (3) | 0.7907 (3) | 0.9504 (3) | 0.0451 (10) | |
C4 | 0.7676 (3) | 0.6938 (3) | 0.8364 (3) | 0.0412 (10) | |
C5 | 0.6222 (3) | 0.6424 (3) | 0.8545 (3) | 0.0510 (10) | |
C6 | 0.5977 (3) | 0.6814 (3) | 0.9860 (3) | 0.0485 (10) | |
C7 | 0.6867 (3) | 0.8151 (4) | 1.2374 (4) | 0.0632 (11) | |
C8 | 1.0285 (3) | 0.7830 (3) | 0.4919 (3) | 0.0656 (12) | |
C9 | 0.9164 (3) | 0.6974 (3) | 0.5505 (3) | 0.0472 (11) | |
C10 | 0.8065 (3) | 0.5478 (3) | 0.4858 (3) | 0.0439 (10) | |
C11 | 0.7337 (3) | 0.5245 (3) | 0.5854 (3) | 0.0453 (10) | |
C12 | 0.6109 (3) | 0.3810 (3) | 0.5722 (3) | 0.0610 (11) | |
C13 | 0.6815 (3) | 0.0924 (3) | −0.0359 (3) | 0.0535 (11) | |
C14 | 0.7177 (3) | 0.1950 (3) | 0.0998 (3) | 0.0491 (11) | |
C15 | 0.7907 (3) | 0.3529 (3) | 0.1308 (3) | 0.0427 (10) | |
C16 | 0.8279 (3) | 0.4020 (3) | 0.0261 (3) | 0.0489 (10) | |
C17 | 0.7911 (3) | 0.2965 (4) | −0.1089 (3) | 0.0525 (11) | |
C18 | 0.7158 (3) | 0.1391 (4) | −0.1433 (3) | 0.0515 (11) | |
C19 | 0.6741 (4) | 0.0239 (4) | −0.2916 (3) | 0.0775 (14) | |
H2 | 0.93830 | 0.89750 | 1.15860 | 0.0590* | |
H3 | 0.98070 | 0.82840 | 0.93820 | 0.0540* | |
H5 | 0.54180 | 0.58170 | 0.77750 | 0.0610* | |
H6 | 0.50120 | 0.64400 | 0.99820 | 0.0580* | |
H8A | 1.08910 | 0.88160 | 0.56310 | 0.0980* | |
H8B | 0.97580 | 0.80210 | 0.41590 | 0.0980* | |
H8C | 1.09280 | 0.72070 | 0.45900 | 0.0980* | |
H12A | 0.62650 | 0.36120 | 0.65720 | 0.0910* | |
H12B | 0.61400 | 0.29190 | 0.49650 | 0.0910* | |
H12C | 0.51390 | 0.39800 | 0.55440 | 0.0910* | |
H13 | 0.63170 | −0.01320 | −0.05630 | 0.0640* | |
H14 | 0.69370 | 0.15930 | 0.16990 | 0.0590* | |
H16 | 0.87840 | 0.50740 | 0.04650 | 0.0590* | |
H17 | 0.81750 | 0.33180 | −0.17860 | 0.0630* | |
H19A | 0.74410 | −0.03650 | −0.30330 | 0.1160* | |
H19B | 0.67840 | 0.08040 | −0.35390 | 0.1160* | |
H19C | 0.57320 | −0.04540 | −0.31190 | 0.1160* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.076 (2) | 0.121 (3) | 0.072 (2) | 0.0077 (19) | 0.0313 (18) | 0.025 (2) |
N2 | 0.0430 (14) | 0.0440 (15) | 0.0477 (15) | 0.0087 (12) | 0.0110 (11) | 0.0132 (12) |
N3 | 0.0484 (14) | 0.0430 (14) | 0.0551 (16) | 0.0059 (12) | 0.0134 (12) | 0.0165 (13) |
N4 | 0.0475 (15) | 0.0521 (15) | 0.0481 (15) | 0.0158 (12) | 0.0123 (12) | 0.0173 (13) |
N5 | 0.0497 (15) | 0.0490 (15) | 0.0535 (16) | 0.0158 (12) | 0.0151 (12) | 0.0180 (13) |
C1 | 0.0472 (18) | 0.0472 (18) | 0.0522 (19) | 0.0155 (15) | 0.0173 (15) | 0.0174 (15) |
C2 | 0.0431 (17) | 0.0463 (18) | 0.0502 (19) | 0.0086 (14) | 0.0068 (14) | 0.0141 (15) |
C3 | 0.0374 (16) | 0.0421 (17) | 0.0536 (19) | 0.0094 (13) | 0.0135 (14) | 0.0154 (15) |
C4 | 0.0387 (16) | 0.0363 (16) | 0.0485 (18) | 0.0123 (13) | 0.0122 (13) | 0.0139 (13) |
C5 | 0.0370 (16) | 0.0517 (19) | 0.0565 (19) | 0.0087 (14) | 0.0058 (14) | 0.0154 (15) |
C6 | 0.0347 (16) | 0.0499 (18) | 0.063 (2) | 0.0103 (14) | 0.0153 (15) | 0.0237 (16) |
C7 | 0.0506 (19) | 0.069 (2) | 0.067 (2) | 0.0119 (17) | 0.0196 (17) | 0.023 (2) |
C8 | 0.059 (2) | 0.059 (2) | 0.068 (2) | 0.0042 (16) | 0.0142 (17) | 0.0196 (17) |
C9 | 0.0426 (17) | 0.0505 (19) | 0.0508 (19) | 0.0147 (15) | 0.0129 (14) | 0.0203 (15) |
C10 | 0.0414 (16) | 0.0433 (17) | 0.0459 (18) | 0.0124 (14) | 0.0084 (13) | 0.0163 (14) |
C11 | 0.0414 (16) | 0.0394 (17) | 0.0513 (18) | 0.0095 (14) | 0.0053 (14) | 0.0162 (15) |
C12 | 0.0584 (19) | 0.0524 (19) | 0.064 (2) | 0.0060 (16) | 0.0102 (16) | 0.0205 (16) |
C13 | 0.0495 (18) | 0.0408 (17) | 0.064 (2) | 0.0116 (14) | 0.0099 (15) | 0.0144 (16) |
C14 | 0.0513 (17) | 0.0503 (19) | 0.0525 (19) | 0.0181 (15) | 0.0195 (14) | 0.0225 (16) |
C15 | 0.0384 (16) | 0.0413 (17) | 0.0439 (17) | 0.0131 (14) | 0.0071 (13) | 0.0103 (14) |
C16 | 0.0436 (17) | 0.0420 (17) | 0.058 (2) | 0.0093 (14) | 0.0098 (14) | 0.0180 (16) |
C17 | 0.0536 (18) | 0.061 (2) | 0.0474 (19) | 0.0212 (16) | 0.0125 (15) | 0.0229 (16) |
C18 | 0.0464 (17) | 0.054 (2) | 0.0510 (19) | 0.0232 (16) | 0.0034 (14) | 0.0130 (16) |
C19 | 0.087 (3) | 0.075 (2) | 0.057 (2) | 0.028 (2) | 0.0109 (19) | 0.0069 (19) |
Geometric parameters (Å, º) top
N1—C7 | 1.139 (5) | C15—C16 | 1.371 (4) |
N4—N5 | 1.252 (3) | C16—C17 | 1.375 (4) |
N2—C4 | 1.418 (3) | C17—C18 | 1.382 (5) |
N2—N3 | 1.383 (4) | C18—C19 | 1.508 (4) |
N3—C9 | 1.316 (3) | C2—H2 | 0.9300 |
N4—C10 | 1.395 (4) | C3—H3 | 0.9300 |
N5—C15 | 1.428 (4) | C5—H5 | 0.9300 |
C1—C2 | 1.387 (4) | C6—H6 | 0.9300 |
C1—C6 | 1.380 (4) | C8—H8A | 0.9600 |
C1—C7 | 1.437 (5) | C8—H8B | 0.9600 |
C2—C3 | 1.373 (4) | C8—H8C | 0.9600 |
C3—C4 | 1.377 (4) | C12—H12A | 0.9600 |
C4—C5 | 1.392 (4) | C12—H12B | 0.9600 |
C5—C6 | 1.369 (4) | C12—H12C | 0.9600 |
C8—C9 | 1.489 (4) | C13—H13 | 0.9300 |
C9—C10 | 1.414 (4) | C14—H14 | 0.9300 |
C10—C11 | 1.366 (4) | C16—H16 | 0.9300 |
N2—C11 | 1.350 (4) | C17—H17 | 0.9300 |
C11—C12 | 1.503 (4) | C19—H19A | 0.9600 |
C13—C14 | 1.372 (4) | C19—H19B | 0.9600 |
C13—C18 | 1.378 (4) | C19—H19C | 0.9600 |
C14—C15 | 1.387 (4) | | |
| | | |
N1···C12i | 3.327 (5) | H3···C13vii | 3.0100 |
N5···C8 | 3.037 (4) | H3···C14vii | 2.9500 |
N1···H12Ai | 2.9300 | H3···C15vii | 3.0600 |
N1···H8Aii | 2.7900 | H5···C11 | 2.8800 |
N3···H3 | 2.4900 | H5···C12 | 2.6400 |
N3···H19Aiii | 2.7100 | H5···H12A | 2.4300 |
N4···H14 | 2.5300 | H5···H12C | 2.3500 |
N4···H5iv | 2.9400 | H5···N4iv | 2.9400 |
N4···H12B | 2.6600 | H6···C6i | 3.0400 |
N5···H8B | 2.8600 | H6···C14iv | 3.0600 |
N5···H8C | 2.8800 | H6···C15iv | 2.8700 |
C5···C12 | 3.144 (4) | H6···C16iv | 2.9600 |
C6···C6i | 3.590 (4) | H8A···N1ii | 2.79 |
C6···C14iv | 3.517 (4) | H8A···C7ii | 3.0000 |
C6···C15iv | 3.561 (4) | H8B···N5 | 2.8600 |
C8···N5 | 3.037 (4) | H8C···N5 | 2.8800 |
C12···N1i | 3.327 (5) | H8C···C10vii | 3.0800 |
C12···C5 | 3.144 (4) | H8C···C11vii | 3.0800 |
C14···C6iv | 3.517 (4) | H12A···C4 | 2.9400 |
C15···C6iv | 3.561 (4) | H12A···C5 | 2.8000 |
C16···C16v | 3.518 (4) | H12A···C17vi | 3.0000 |
C2···H16vi | 3.0100 | H12A···H5 | 2.4300 |
C4···H12A | 2.9400 | H12A···H17vi | 2.4200 |
C5···H12A | 2.8000 | H12A···N1i | 2.93 |
C5···H13iii | 3.0500 | H12B···N4 | 2.6600 |
C5···H12C | 3.0800 | H12B···H19Cix | 2.5300 |
C6···H13iii | 2.9900 | H12C···C5 | 3.0800 |
C6···H6i | 3.0400 | H12C···H5 | 2.3500 |
C7···H8Aii | 3.0000 | H12C···C11iv | 2.9200 |
C10···H8Cvii | 3.0800 | H12C···H12Civ | 2.5600 |
C11···H8Cvii | 3.0800 | H13···C5x | 3.0500 |
C11···H12Civ | 2.9200 | H13···C6x | 2.9900 |
C11···H5 | 2.8800 | H13···H19C | 2.5400 |
C12···H5 | 2.6400 | H14···N4 | 2.5300 |
C13···H3vii | 3.0100 | H16···C2viii | 3.0100 |
C14···H3vii | 2.9500 | H16···C16v | 2.9600 |
C14···H6iv | 3.0600 | H16···C17v | 3.0500 |
C15···H3vii | 3.0600 | H17···H12Aviii | 2.4200 |
C15···H6iv | 2.8700 | H17···H19B | 2.3900 |
C16···H6iv | 2.9600 | H19A···N3x | 2.7100 |
C16···H16v | 2.9600 | H19B···H17 | 2.3900 |
C17···H12Aviii | 3.0000 | H19C···H13 | 2.5400 |
C17···H16v | 3.0500 | H19C···H12Bix | 2.5300 |
H3···N3 | 2.4900 | | |
| | | |
N3—N2—C4 | 117.5 (2) | C17—C18—C19 | 121.4 (3) |
N3—N2—C11 | 111.6 (2) | C1—C2—H2 | 120.00 |
C4—N2—C11 | 131.0 (3) | C3—C2—H2 | 120.00 |
N2—N3—C9 | 105.0 (2) | C2—C3—H3 | 120.00 |
N5—N4—C10 | 115.2 (3) | C4—C3—H3 | 120.00 |
N4—N5—C15 | 113.7 (2) | C4—C5—H5 | 120.00 |
C2—C1—C6 | 119.7 (3) | C6—C5—H5 | 120.00 |
C2—C1—C7 | 121.0 (3) | C1—C6—H6 | 120.00 |
C6—C1—C7 | 119.4 (3) | C5—C6—H6 | 120.00 |
C1—C2—C3 | 119.9 (3) | C9—C8—H8A | 109.00 |
C2—C3—C4 | 120.4 (3) | C9—C8—H8B | 109.00 |
N2—C4—C3 | 119.0 (3) | C9—C8—H8C | 110.00 |
N2—C4—C5 | 121.3 (3) | H8A—C8—H8B | 109.00 |
C3—C4—C5 | 119.7 (3) | H8A—C8—H8C | 109.00 |
C4—C5—C6 | 119.9 (3) | H8B—C8—H8C | 109.00 |
C1—C6—C5 | 120.4 (3) | C11—C12—H12A | 109.00 |
N1—C7—C1 | 179.1 (4) | C11—C12—H12B | 109.00 |
N3—C9—C8 | 119.6 (3) | C11—C12—H12C | 110.00 |
N3—C9—C10 | 110.9 (3) | H12A—C12—H12B | 109.00 |
C8—C9—C10 | 129.6 (3) | H12A—C12—H12C | 110.00 |
N4—C10—C9 | 133.1 (3) | H12B—C12—H12C | 109.00 |
N4—C10—C11 | 120.9 (3) | C14—C13—H13 | 119.00 |
C9—C10—C11 | 106.0 (3) | C18—C13—H13 | 119.00 |
N2—C11—C10 | 106.6 (3) | C13—C14—H14 | 121.00 |
N2—C11—C12 | 125.9 (3) | C15—C14—H14 | 120.00 |
C10—C11—C12 | 127.6 (3) | C15—C16—H16 | 120.00 |
C14—C13—C18 | 122.8 (3) | C17—C16—H16 | 120.00 |
C13—C14—C15 | 119.0 (3) | C16—C17—H17 | 119.00 |
N5—C15—C14 | 125.0 (3) | C18—C17—H17 | 119.00 |
N5—C15—C16 | 115.6 (3) | C18—C19—H19A | 109.00 |
C14—C15—C16 | 119.4 (3) | C18—C19—H19B | 109.00 |
C15—C16—C17 | 120.5 (3) | C18—C19—H19C | 109.00 |
C16—C17—C18 | 121.4 (3) | H19A—C19—H19B | 110.00 |
C13—C18—C17 | 117.0 (3) | H19A—C19—H19C | 109.00 |
C13—C18—C19 | 121.7 (3) | H19B—C19—H19C | 109.00 |
| | | |
C4—N2—N3—C9 | 179.2 (2) | C2—C3—C4—C5 | 2.4 (4) |
C11—N2—N3—C9 | 1.0 (3) | N2—C4—C5—C6 | 179.7 (3) |
N3—N2—C4—C3 | −28.3 (4) | C3—C4—C5—C6 | −3.5 (4) |
N3—N2—C4—C5 | 148.5 (3) | C4—C5—C6—C1 | 2.3 (5) |
C11—N2—C4—C3 | 149.5 (3) | N3—C9—C10—N4 | −180.0 (3) |
C11—N2—C4—C5 | −33.7 (5) | N3—C9—C10—C11 | 0.0 (3) |
N3—N2—C11—C10 | −1.0 (3) | C8—C9—C10—N4 | −0.2 (6) |
N3—N2—C11—C12 | 177.1 (3) | C8—C9—C10—C11 | 179.8 (3) |
C4—N2—C11—C10 | −179.0 (3) | N4—C10—C11—N2 | −179.4 (2) |
C4—N2—C11—C12 | −0.9 (5) | N4—C10—C11—C12 | 2.5 (5) |
N2—N3—C9—C8 | 179.6 (2) | C9—C10—C11—N2 | 0.6 (3) |
N2—N3—C9—C10 | −0.6 (3) | C9—C10—C11—C12 | −177.4 (3) |
C10—N4—N5—C15 | 179.2 (2) | C18—C13—C14—C15 | 0.6 (5) |
N5—N4—C10—C9 | −4.9 (5) | C14—C13—C18—C17 | 0.6 (5) |
N5—N4—C10—C11 | 175.1 (3) | C14—C13—C18—C19 | −179.8 (3) |
N4—N5—C15—C14 | −17.4 (4) | C13—C14—C15—N5 | 179.1 (3) |
N4—N5—C15—C16 | 163.2 (3) | C13—C14—C15—C16 | −1.5 (4) |
C6—C1—C2—C3 | −1.2 (4) | N5—C15—C16—C17 | −179.4 (3) |
C7—C1—C2—C3 | 178.8 (3) | C14—C15—C16—C17 | 1.1 (4) |
C2—C1—C6—C5 | 0.1 (4) | C15—C16—C17—C18 | 0.2 (5) |
C7—C1—C6—C5 | −179.9 (3) | C16—C17—C18—C13 | −1.0 (4) |
C1—C2—C3—C4 | 0.0 (4) | C16—C17—C18—C19 | 179.4 (3) |
C2—C3—C4—N2 | 179.3 (3) | | |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+2, −z+2; (iii) x, y+1, z+1; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+1, −z; (vi) x, y, z+1; (vii) −x+2, −y+1, −z+1; (viii) x, y, z−1; (ix) −x+1, −y, −z; (x) x, y−1, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cg1iv | 0.93 | 2.82 | 3.533 (3) | 135 |
C3—H3···Cg2vii | 0.93 | 2.79 | 3.464 (3) | 131 |
Symmetry codes: (iv) −x+1, −y+1, −z+1; (vii) −x+2, −y+1, −z+1. |
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